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Book Report: Bossypants by Tina Fey

Memoir is an incredibly difficult genre to write well. It requires a certain level of narcissism mixed with transcendent wisdom that must be shared with the world. Because Tina Fey lacks both of these qualities, Bossypants is a hilarious, relatable look into the unlikely success of one of the funniest women on the planet.

The self-depreciating tone of the book told with Tina Fey’s signature sarcastic wit struck a chord with the insecure middle school nerd of my past. As a (kind of) successful (though far less famous) woman myself, I realized how important that nerd and all of her embarrassing, awkward moments were in forming who I am now. To look back on our past selves and be able to endearingly chide ourselves instead of reliving that embarrassment is an important step in loving yourself. Forgiving our child selves, and acknowledging the strength that pushed us through the mess of adolescence is an indicator of growth. Tina Fey recounts an awkward time in her life where she used her gay friends as props, but selfishly wanted them to stay “half in the closet.” This analysis of her past was no doubt a huge epiphany for her that helped her form stronger relationships and become a better person.

“You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.” ― Tina Fey, Bossypants

Tina Fey also failed a lot. Sometimes her sketches fell flat. Sometimes she didn’t feel like her work was complete when the SNL deadline hit and she had to forge ahead anyway. Her insight on the myth of doneness resonated. There will occasionally be times when the goal changes from finishing to fighting through it and moving on to the next thing. There’s no time to beat yourself up over failures, but there’s immense value in learning from them and applying them to the next sketch.

“Don’t waste your energy trying to educate or change opinions; go over, under, through, and opinions will change organically when you’re the boss. Or they won’t. Who cares? Do your thing, and don’t care if they like it.”
― Tina Fey, Bossypants

I also appreciate her openness about doubt and anxiety. No successful woman achieved her dreams without doubting herself along the way. Staving off the “what ifs” that anxiety chronically throws at me is one of my biggest challenges. Tina Fey laid bare all of her doubts about motherhood, comedy, cruises, fame, even her writing and acting abilities. But she never questioned the talent of her team.

I’m sure each of her peers have felt the same doubts, but there was a huge lesson here, especially for women: Others see us much differently than we see ourselves. It’s important to share our perspective with the women in our lives. Fey is hyper-aware of the pressure on women to not only succeed, but “do it all.” I was nodding my head in agreement with her thoughts on older women (especially those who speak their minds) being referred to as “crazy.” Where age = wisdom for men, as women we lose our credibility and relevancy when we’re no longer “hot.” Amy Schumer actually did a hysterical sketch with Tina Fey on this phenomenon:

Reading about the hilarious behind-the-scenes work on SNL and 30 Rock makes me want to watch all of 30 Rock. I think I fell off somewhere around the time the latest season of Shameless appeared on Netflix. Putting together a tv show seems unimaginably stressful, triple that for a live show! My admiration for Tina Fey has grown exponentially.

Her appreciation and gratitude for the people in her life, especially Amy Poehler, inspired me to write love letters to my friends.

Do you want a love letter? DM me your address on Instagram or Twitter and I’ll send you a handwritten note about how much ass you kick.